Where Hobos Roam | Midwest Living

Where Hobos Roam

"What other town would embrace a bunch of hobos for over 100 years?" asks petite Connecticut Shorty (who retired after logging 5,000 free miles) while looking at the small-town Iowa surroundings. City leaders lured the quirky festival to town in 1900 to get publicity, but hobos and the curious still trek to the north-central town of Britt for the National Hobo Convention the second week of August each year. 

Much of the convention is a typical town festival, where locals wait in line for carnival rides, slices of homemade pie and cups of beer. And then there's the hobo-theme portion, including a parade where three dozen self-described hobos wave to crowds from a float.

While the meaning of hobo is debated, proud titleholders are quick to explain they are workers hitching rides on freight trains, not bums grubbing for handouts. Whether motivated by financial need or a sense of adventure, they have a community spirit and earn nicknames during their travels.

One festival attendee, nicknamed Frog, worked in Louisiana oil rigs, Washington orchards and Catskills motels during his 31 years of train hopping. “It was absolute total freedom,” the 64-year-old says.

Tramp Printer, now 77, rode trains to work at newspaper printing presses in the 1950s. He first visited Britt in 1983 after reading about it in a magazine he printed. “It’s like a family,” he says.

And just like every other one, this family has its traditions. One is sharing free mulligan stew that simmers in 55-gallon metal barrels.

After lunch: the coronation of Hobo King and Queen. The audience votes by applause, and this year, the coffee-can crowns go to Songbird and Fast Talkin’ Twin City Cindy Lou.

Get to know past hobo royalty at the display of paintings by local artist Leanne Marlow Castillo. “Their lives are in their faces,” she says. “Fascinating faces and stories.” The paintings are displayed during the convention.

Or hear their stories at the Hobo Jungle campsite, a park dotted with modern tents and campers by the railroad tracks. At night, the jungle comes alive with the sounds of harmonicas, guitars and recorders. But the music stops for tonight’s rare hobo wedding. Czech Hobo’s bride walks under an arch of walking sticks held high by former hobo queens. The couple carries rhubarb as they circle the campfire. In true hobo matrimonial tradition, they throw the poisonous leaves into the flames to extinguish bad influences and keep the stalk for a fruitful marriage.

Not too far from the wedding, a more somber ceremony takes place. Friends lay bandanas and flowers on gravestones at the National Hobo Cemetery, part of the local cemetery grounds. Sidedoor Pullman Kid wanted to be buried here, but ended up in a pauper’s grave in Arizona. This year, the hobo community raised $3,500 to lay the former Hobo King to rest in Britt. A breeze rustles aluminum can wind chimes at the cemetery. One can almost hear the distant whistle of a train.

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